Gregory joined John Polands, a large Members’ Agent in 1986. He also worked for Caudle Hilsum, Scott Caudle Hilsum and Vantage before joining Wren in 1994. In 2000, Gregory joined Hampden Agencies Ltd and was a Director of Hampden Private Capital. Gregory is a Private Client Director and has set up a number of corporate Vehicles for Ark, Atrium, Cathedral, Heritage (now Argo), Illium (now HCC) and MAP. Gregory also looks after a number of influential members of Lloyd’s. He is a member of Hampden Underwriting Research's committee.